The Lucky One
by IoIngridWeaver
Summary: Dan Humphrey is back in NYC after a nineteen year absence determined to start anew amidst the ashes of his crumbling marriage. In tow he has his children who are more than a handful. But when one pulls a stunt that draws the attention of the entire UES he will have to face everyone he left behind, including the woman he hates with a passion and maybe never stopped loving.
1. Chapter 1

**Title: The Lucky One**

**Summary: ****It has been almost nineteen years since Dan set foot in New York City after he fled the Upper East Side when he was twenty-one. Now forty Dan is following in his father's footsteps; divorcing his wayward wife, living in the loft, and struggling to raise his children in the city that broke him. But when his daughter pulls a stunt worthy of the record books everything and everyone Dan left behind comes crashing back into his fragile life with a vengeance. Now Dan must contend with broken friendships, long buried love triangles, and secrets that were better off left in the past where he feels they belong. But none of this seems to matter as his children begin to pay for the choices he made and his wife comes back into his life determined to take the children. Now left fighting for the only things that matter Dan receives help from an unlikely source, the woman he hated for years and the one he is sure he is never truly stopped loving. But if they are ever going to have a chance at anything she is going to half to step up and prove to Dan once and for all she can take a back seat to his family and get past her own insecurities and demons.**

**Dan Humphrey sometimes wonders if this was always his fate from the beginning. Sometimes he wonders if he was always doomed to follow in his father footsteps. Here he is; forty, abandoned by his wife, and struggling to raise his children in the very same loft where he was raised while his father lives on the floor above. His younger sister is living in Boston working as a fashion designer while he wife is god knows where. **

**He should have seen it coming. As soon as she said she was taking off to find herself the alarm bells should have gone off in his head. But no he had been too preoccupied with the death of his best friend leaving his eldest son without a mother and his younger children without their godmother. **

**When Dan Humphrey got married when he was twenty-four the only people in attendance were Rufus, Jenny, Georgina, Milo, and his bride to be Clare Higgins. Flash foreword sixteen years later and Dan Humphrey has had no contact with the UES since she was twenty-two. He is an accomplished writer and the editor of the LA Times. He had moved out west for his wife and his children were born and raised by the Pacific Ocean. **

**Now everything has changed. He has moved back to the city he fled to become editor of the NY Times in order to try and provide his children with everything they deserve. And they deserve their grandfather and aunt. So he moves back to where he grew up and watches as his children struggle to live without their mother. **

**There is twenty-one year old Milo Rufus with his mother's eyes and hair and Dan's passion for writing with his mother's nose for trouble. Adopted by Dan when he was six Milo is his son in every way that counts. But still he has that spark his mother had that attracts trouble like moths to a flame. More than one Dan has had to pull Milo out of a fight or bail his out of jail since he turned sixteen. And Milo is more like Dan than anyone ever saw coming when he arrived in LA three years prior with a ten week old baby and a letter from the mother saying she could not raise her child. So Dan became a grandfather and a back up parent to now three year old Addison Sabrina Humphrey.**

**Philippa Lorraine aka Pippa is fourteen, precocious, and cunning with her mother's cornflower blue eyes and his dark curls. She is small and compact but has a darkness in her Dan sees similar to the one Jenny had. But unlike Jenny Pippa is dedicated to her family and is like a snake in some ways. She moves slow and lethargically but has poison on her tongue and will hiss at you if you get in her way. **

**And his youngest, Jacob George Tyler, has his mothers bright blonde hair with Dan's dark eyes and is one of the most energetic children Dan has ever seen. He bounces from one thing to another and can never sit still. He is curious and constantly asking questions and always has his nose in a book. At age nine he is already close to doing high school work. With his photographic memory and thirst for knowledge Jake is Dan is many ways. But he has also inherited his mother's passion for sports and plays soccer, baseball, and rugby with a finesse and energy Dan could never quite understand. **

**And then there his Addison; Addy, the pride and joy of Milo and the apple of eyes of both Dan and Rufus. With her green eyes, chocolate brown hair, pale skin, freckles, and her grandmother's spark in her eyes Addy Humphrey is spoilt and has them all wrapped around her little finger. And what was worse is than she and everyone else knew it. **

**Dan does not like to think himself too vain. But he is forty and he knows he is too young to be a grandfather. But here he is helping to raise a precocious little girl who he loves more than he ever thought he could. Milo never talks about her mother and Dan never asks. Never once has she tried to become involved in Addy's life and that suit's the Humphrey clan just fine. **

**And now he is struggling to hold said toddler in his arms as Milo stands at the counter paying for his daughter's bail. Jake is holding onto the corner of Dan's plaid shirt as he raises his eyes to the ceiling and tries to no lose his cool. He loves his daughter. He loves his daughter. His daughter is now grounded till the days she turns ninety. **

**He loves his daughter. He really does. But Pippa, when she gets hooked on something, takes it to extremes until she moves onto her next obsession. And lately, thanks mainly part to her Aunt Vanessa's influence, (sometimes Dan wonders why Vanessa had to go all hippie and tree hugger and live on a commune in the middle of Oklahoma of all places? But he loves his friend and knows that whenever she can pull herself away from saving the world and visit it is a highlight of his lives and those of his kids. So he puts up with her pushing to go green and the injustice of the world and her shoving down his throat her documentaries on global warming and the like) Pippa has brought it upon herself to change the fashion industry one label at a time from using fur. **

**Now Jenny is safe from the wrath of her niece due to her distain for fur. But this was taking it way to far. His daughter dumping a can of pain on a red carpet event during New York Fashion Week? Way, way too far. **

**He sighs as Addy tries to squirm out of his arms once more turning as Milo approaches him with Pippa behind him. Dan says nothing as she meets his stare. He knows it will only make the situation worse. He simply arches his eyebrow to which she shrugs and smirks. He then shakes his head but can't stop the smile from appearing on his face. She is his daughter after all. And she is the god daughter of Georgina Sparks. He should have known better than to ever think she would be tame. **

**Just as they turn to go a voice screeching for justice for her Chanel coat and Prada bag stops him in his tracks. It has been almost nineteen years since he heard that voice. It has been so long since he has even thought about her. He has longer gotten over whatever he felt for her. He is loathsome to turn around because he knows once he does he will no longer be able to pretend she is just a figment of his imagination. But when he hears Pippa screaming at her about cruelty to animals he knows he has to act. **

**Turning around he sees her there in all of her glory, covered head to toe in bright green paint, as she goes head to toe with his daughter. Milo come up to his side and takes Addy from his arms and pulls Jake back by his coat. **

**Dan then goes foreword and places himself between Blair and his daughter. Pippa is small, the top of her head barely touches Dan's shoulder, but Blair is only an inch shorter than him in her heels. Pippa is about to scream more but everything comes screeching to a halt when Blair looks at him with her mother gaping open like a fish. **

**Dan does not know what she is thinking but he does not care. He stopped caring about what Blair Waldorf turned Bass thought about him the day she broke his heart. So he apologizes, says he will pay for the damage, and grabbing his daughter by the arm to walk away. **

**He walks quickly with Pippa dragging herself behind him and Milo beside him with the kids. Dan wants to get away quickly. He wants to get away from Blair and her eyes and the emotions within. The betrayal and the anger and the shock in her eyes. But most of all he wants to get away from those deep doe eyes and the emotion that looks too much like the one he used to stare at her with back when he loved her more than anything. **

**But as Pippa's phone beeps and she announces they are on Gossip Girl Dan knows he can no longer run from his past. And he can't uproot his family up again after barely four months in the city. So he will have to suck it up and deal with it like he always has. Because no matter what his family needs him. She doesn't. Blair made her choice. No matter how much it destroyed him all those long years ago. **


	2. Chapter 2

"**And they tell you that you're lucky.**

**But you're so confused,**

**Cause you don't feel pretty, you just feel used.**

**And all the young things line up to take your place.**

**Another name goes up in lights. **

**You wonder if you'll make it out alive**

**And they'll tell you now, you're the lucky one.**

**Yeah, they'll tell you now, you're the lucky one.**

**Can you tell me now, you're the lucky one, oh, oh, oh."-Taylor Swift ****The Lucky One**

The day Dan turned 21 he was met upon a sight that destroyed him. The sight of his girlfriend and one Chuck Bass caught in a passionate embrace in her apartment. Their lips locked, clothes thrown across the floor, making out on the couch they had just watched movies on the night before.

He must have made a sound because the next thing he knew Blair was standing in front of him begging him to listen to him. Chuck, of all people, was apologizing saying that it was a mistake and that it meant nothing.

The next thing Dan did was punch the living day lights out of Chuck, turn on his heel, and walk down the hallway towards the elevator all the while ignoring Blair Waldorf's pleas for him to listen and not to leave her. Dan's response was to get inside the elevator, spit at her bare feet, and say nothing as the doors closed.

He leaves the city for Detroit barely three hours later with nothing but the clothes on his back and a broken heart. He holes up in a dingy motel and spends the next week ignoring his phone and only calls his father and sister to let them know he is alive and well.

One weeks after he arrives he called Alessandra to inform her he has completed his next novel and is working on a companion piece. He faxes it to her and after she reads it a few hours later she asks him if he is sure he wants to publish this. He says he is and gives her the go-ahead to shop it around.

Meanwhile he goes out west and finds himself in San Diego where he finds a single Georgina Sparks and Milo, the boy who should have been his. Moving in with the girl who was his rock that summer in Rome Dan tries to rebuild his life and gets a job at a bookstore all the while churning out as much writing as he can. It is when Dan is twenty-two he meets twenty-four year old Claire Higgins.

Claire is everything Blair is not; blonde, muscular, funny, compassionate, and kind. She is the daughter of basketball legend Hector Higgins and a legend in her own right for competing in two events during the London 2012 Olympics. Claire chases him and that in and unto itself is the appeal. She wants him; all of him and she is not willing to take no for an answer.

She knows who he is and understands that he will need some time. They begin to date and she ever accepts his plan to one day adopt Milo and she is approved by Jenny and Rufus and Georgina whom can find no dirt on her whatsoever.

He proposes when he is twenty-four and they marry on the beach one week later. After Dan finally finishes his degree from UCLA. He his English Masters and sets out teaching at a local college while writing on the side.

When he is twenty-five Dan Humphrey becomes a father when the adoption goes through and Georgina officially moves next door to them on the beach where Dan learns to surf and tries to be as fit and active as Claire. While will never a Wilt Chamberlin Dan soon begins to appreciate it. He loves to run and clear his head and hear nothing but the ocean and hit feet hitting the pavement or the sand. He discovers a passion for soccer that has him coaching Milo's junior league team where Claire cheers restrained compared to his mother who screams at the refs and is kicked off of the field more times than he can count.

Just before he turns twenty-six and Clair turns twenty-eight during a routine checkup they discover she is almost three months pregnant. Although neither is prepared for a baby nor was it planned both are overjoyed and soon begin to prepare for the baby.

Claire is the only child of dead parents with hardly any living family while Dan's is located in NYC and in London so aside from Georgina it becomes apparent they are on their own. He buys all of the books and baby proofs their house and buys a minivan and does everything he is supposed to. He expects it to not be easy but even he does not except what comes.

The pregnancy is not easy. Morning sickness plagues the entire pregnancy and Milo is having trouble adjusting and something is wrong. They all feel it; waiting for the other shoe to drop. It happens when Claire is seven months pregnant. She begins to bleed and hemorrhage and almost miscarries before they get to the hospital where an emergency C-Section reveals his daughter. She is barely three pounds and looks nothing like he thought she would.

But staring at her in the NICU Dan vows to protect her from anything and everything in the world that could harm her and stays by Claries' side as she struggles to heal. They name her Philippa after they find it randomly in a baby book. Lorraine was her mother's name and Dan thinks it is better than his own mother's name.

A weeks after his daughter is born Dan is in the hospital when he sees a bouquet on the table next to his sleeping daughter and upon reading the card he demands to a nurse they be disposed of. He does not even bother to read the message on the card instead devoting his attention to his family.

Dan avoided all contact with the UES and does not return their calls or the imploring texts to come home. He does not invite them to his wedding and sends back or destroys all of the gifts that arrive after his wedding. The only person he relents and contact is Nate thanking him for the congrats and to please not call again.

Dan can't bear to think about everything he has lost. While his heart was healing Dan struggled with the loss of Blair who had finally decided to be with him after he arrived back from Rome and the friendship he had slowly built with chuck over the course of a year. He refuses to even try and talk to Serena or Eric who will side with Chuck as they do with everything and Lily means nothing to him anymore; she is a Bass after all.

So he makes new friends and reconnects with Vanessa after she tracks him down and camps out on his doorstep banging a conga drum until he opens his door, hisses and demands she stop, and is pushed aside when she weasels her way back into his home, life, and heart.

The novel Dan publishes first after he leaves is called _I Left My Heart In San Francisco._ it is a risky novel about a man who falls in love with an addict who eventually leaves him to be with her drug dealer boyfriend and descends into a world she can't seem to escape until it is almost too late. She arrives on her old lover's doorstep to try and reconcile only to find out he has moved on. He slams the door in her face leaving her out in the cold on New Year's Eve. She watches through the front window as he celebrates with his family. It becomes a best seller and is acclaimed.

The next is called _Falling Skies. _The protagonist enters into a marriage of conveyance with the best friend of his one time lover only to find out she is still seeing her ex as well. This continues for a decade until he divorces her, takes their children, and leaves her with nothing while he struggles to move on. It shoots up the lists and is ripped off of shelves quicker than it can be printed.

And it goes like this. All have a common theme. Claire does not mention it nor does Alessandra or his publisher. Georgina mentions it but he brushes it off as nothing.

He has a few blunders and becomes a children's author once he adopts Milo. But one day while watching the ocean he becomes inspired to write a trilogy that will becomes his masterpiece.

The _City Trilogy _begins with _City of Bones _during the French Revolution. It is the story of a young soldier who falls in love with a woman forbidden to him; a disposed noble's daughter who returns his affections but chooses another in order to secure wealth and an epic love that occurs only in legends and stories. The novel ends with the soldier traveling to England to try and discover his fortune. He channels everything into the novel; his inadequacy, his pain, his love, his hatred, and his hope for a better future. It does not sell all that well but much to his shock and awe is nominated for a Pulitzer. It is his crowning glory until he turns thirty and they decide they want to try and have another child.

Whenever Dan thinks of Blair all that he feels is hatred and pity. Pity she is so pathetic and so weak. Pity that she had tied herself to Chuck Bass for the rest of her life mere months after he left NYC.


End file.
